Dicyclohexylcarbodiimide → HCID 86653389, compound

HRID 1192775Notes

Reaction equation

HRID 1192775 reaction equation
[CH3:1][O:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5](/[CH:10]=[CH:11]/[C:12]([CH2:14][C:15](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:24]([O:25][CH3:26])[C:22]([OH:23])=[CH:21][CH:20]=2)=[O:16])=[O:13])[CH:4]=1.[C:28](O)(=[O:50])/[CH:29]=[CH:30]\[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[C:28]([O:9][C:8]1[CH:7]=[CH:6][C:5]([CH:10]=[CH:11][C:12](=[O:13])[CH2:14][C:15](=[O:16])[CH:17]=[CH:18][C:19]2[CH:20]=[CH:21][C:22]([OH:23])=[C:24]([O:25][CH3:26])[CH:27]=2)=[CH:4][C:3]=1[O:2][CH3:1])(=[O:50])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 969516CurcuminHCID 86653387HCID 86653387, compound

Product 1

HCID 86653389HCID 86653389, compoundYield 45.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of curcumin (300 mg, 0.81 mmol), cis-docosahexaenoic acid (275 mg, 0.83 mmol) and catalytic amount of 4-(dimethylamino)pyridine in DCM (10 mL) was added a solution of N,N′-dicyclohexylcarbodiimide (252 mg, 1.2 mmol) in DCM (5 mL) for 5 min at ice cold temperature. The mixture was stirred at rt for 16 h and diluted with water. DCM layer was separated and the aqueous layer was extracted with DCM (3×100 mL). The combined DCM layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and the residue was chromatographed over silica gel column using hexane-ethyl acetate mixture (90:10) as an eluent to give the product as oil (250 mg, 45%). IR (neat) νmax 3015, 2960, 2930, 1761, 1631, 1593, 1269, 1120, 1031, 972 cm−1; 1H NMR (CDCl3) δ 7.61 (1H, d, J=16.0 Hz, H-1), 7.60 (1H, d, J=15.6 Hz, H-7), 7.03-7.16 (5H, m, H-2′, 2″, 5′, 6′, 6″), 6.93 (1H, d, J=8.4 Hz, H-5″), 6.55 (1H, d, J=16 Hz, H-2), 6.49 (1H, d, J=16 Hz, H-6), 5.89 (1H, br s, Ar—OH), 5.83 (1H, s, H-4), 5.38-5.39 (12H, m, H-4′″, 5′″, 7′″, 8′″, 10′″, 11′″, 13′″, 14′″, 16′″, 17′″, 19′″, 20′″), 3.95 (3H, s, Ar—OCH3), 3.87 (3H, s, Ar—OCH3), 2.84-2.86 (10H, m, H-6′″, 9′″, 12′″, 15′″, 18′″), 2.58-2.66 (2H, m, H-2″), 2.22-2.23 (2H, m, H-21″), 2.05-2.09 (2H, m, H-3′″), 0.97 (3H, t, J=7.4 Hz, H-22′″); LCMS (ESI, negative ion mode): m/z 677 (M-H)−.

Workup

  1. customDCM layer was separated
  2. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  3. washThe combined DCM layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-d4b0185cccbf46cfb4db16adae5ef464
Source dataset
uspto-grants-2014_03
Patent number
US08680143B2

Reaction notes

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